Start Here
If you are new to these texts, here is a short and opinionated map.
Read this first
The Tao Te Ching. Eighty-one short chapters, most under a page. Read it straight through in an hour without trying to understand it, then put it down for a week. Understanding is not the first pass's job.
A caution on translations: they differ enormously, because the classical Chinese is compressed almost to the point of ambiguity. Read two. The disagreements between them are informative.
Then this
The Zhuangzi — funnier, stranger, and more argumentative. Where Lao Tzu states, Zhuangzi tells a story and lets you fall into the hole yourself. The first seven chapters ("the Inner Chapters") are the ones to start with.
Three ideas worth carrying
- Wu wei — acting with the grain rather than against it.
- Ziran — self-so-ness; things being what they are without being made to be.
- Pu — the uncarved block; potential that has not yet been narrowed into a single use.
What not to do
Do not try to be a Taoist. There is no membership, and the effort of performing it is exactly the kind of forcing the books spend their whole length warning about.